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Molecules 2018, 23(5), 1225; https://doi.org/10.3390/molecules23051225

Conformational Aspects of the O-acetylation of C-tetra(phenyl)calixpyrogallol[4]arene

Departamento de Química, Facultad de Ciencias, Universidad Nacional de Colombia-sede Bogotá, Carrera 30 # 45-03, Bogotá 111321, Columbia
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Received: 28 April 2018 / Revised: 15 May 2018 / Accepted: 17 May 2018 / Published: 20 May 2018
(This article belongs to the Section Organic Chemistry)
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Abstract

Reaction between pyrogallol and benzaldehyde results in a conformational mixture of C-tetra(phenyl)pyrogallol[4]arene (crown and chair). The conformer mixture was separated using crystallization procedures and the structures were determined using FTIR, 1H-NMR, and 13C-NMR. O-acetylation of C-tetra(phenyl)pyrogallol[4]arene (chair) with acetic anhydride, in pyridine results in the formation of dodecaacetyl-tetra(phenyl)pyrogallol[4]arene. The structure was determined using 1H-NMR and 13C-NMR finding that the product maintains the conformation of the starting conformer. On the other hand, the O-acetylation reaction of C-tetra(phenyl)pirogallol[4]arene (crown) under same conditions proceeded efficiently, and its structure was determined using 1H-NMR and 13C-NMR. Dynamic 1H-NMR of acetylated pyrogallolarene was studied by means of variable temperature in DMSO-d6 solution, and it revealed that two conformers are formed in the solution. Boat conformations for acetylated pyrogallolarene showed a slow interconversion at room temperature. View Full-Text
Keywords: macrocycles; pyrogallolarenes; conformers; acetylation macrocycles; pyrogallolarenes; conformers; acetylation
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Casas-Hinestroza, J.L.; Maldonado, M. Conformational Aspects of the O-acetylation of C-tetra(phenyl)calixpyrogallol[4]arene. Molecules 2018, 23, 1225.

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